A diastereodivergent synthetic strategy for the syntheses of communesin F and perophoramidine

Organic Letters

Volumn 16, Issue 12, 2014, Pages 3316-3319

  Han, Seo Jung ^a   Vogt, Florian ^a   Krishnan, Shyam ^a   May, Jeremy A ^a   Gatti, Michele ^a   Virgil, Scott C ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; COMMUNESIN F; FUSED HETEROCYCLIC RINGS; HALOGENATED HYDROCARBON; PEROPHORAMIDINE;

ALKYLATION; ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PENICILLIUM; STEREOISOMERISM; SYNTHESIS; UROCHORDATA;

ALKALOIDS; ALKYLATION; ANIMALS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HYDROCARBONS, HALOGENATED; MOLECULAR STRUCTURE; PENICILLIUM; STEREOISOMERISM; UROCHORDATA;

EID: 84903171343     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol5013263     Document Type: Article

References (46)

1. Numata, A.; Takahashi, C.; Ito, Y.; Takada, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Imachi, M.; Ito, T.; Hasegawa, T. Tetrahedron Lett. 1993, 34, 2355
2. Ratnayake, A. S.; Yoshida, W. Y.; Mooberry, S. L.; Hemscheidt, T. K. J. Org. Chem. 2001, 66, 8717
3. Retraction of this article was prompted by a revision of structure; see: Ratnayake, A. S.; Yoshida, W. Y.; Mooberry, S. L.; Hemscheidt, T. K. J. Org. Chem. 2003, 68, 1640
4. Jadulco, R.; Edrada, R. A.; Ebel, R.; Berg, A.; Schaumann, K.; Wray, V.; Steube, K.; Proksch, P. J. Nat. Prod. 2004, 67, 78
5. Hayashi, H.; Matsumoto, H.; Akiyama, K. Biosci. Biotechnol. Biochem. 2004, 68, 753
6. Andersen, B.; Smedsgaard, J.; Frisvad, J. C. J. Agric. Food Chem. 2004, 52, 2421
7. Dalsgaard, P. W.; Blunt, J. W.; Munro, M. H. G.; Frisvad, J. C.; Christophersen, C. J. Nat. Prod. 2005, 68, 258
8. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2006, 23, 26
9. Wigley, L. J.; Mantle, P. G.; Perry, D. A. Phytochemistry 2006, 67, 561
10. Verbitski, S. M.; Mayne, C. L.; Davis, R. A.; Concepcion, G. P.; Ireland, C. M. J. Org. Chem. 2002, 67, 7124
11. Denault, J.-B.; Salvesen, G. S. Chem. Rev. 2002, 102, 4489
12. May, J. A.; Zeidan, R. K.; Stoltz, B. M. Tetrahedron Lett. 2003, 44, 1203
13. Crawley, S. L.; Funk, R. L. Org. Lett. 2003, 5, 3169
14. May, J. A.; Stoltz, B. Tetrahedron 2006, 62, 5262
15. Yang, J.; Song, H.; Xiao, X.; Wang, J.; Qin, Y. Org. Lett. 2006, 8, 2187
16. Crawley, S. L.; Funk, R. L. Org. Lett. 2006, 8, 3995
17. Seo, J. H.; Artman, G. D., III; Weinreb, S. M. J. Org. Chem. 2006, 71, 8891
18. Yang, J.; Wu, H.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2007, 129, 13794
19. George, J. H.; Adlington, R. M. Synlett 2008, 2093
20. Siengalewicz, P.; Gaich, T.; Mulzer, J. Angew. Chem., Int. Ed. 2008, 47, 8170
21. Liu, P.; Seo, J. H.; Weinreb, S. M. Angew. Chem., Int. Ed. 2010, 49, 2000
22. Zuo, Z.; Xie, W.; Ma, D. J. Am. Chem. Soc. 2010, 132, 13226
23. Zuo, Z.; Ma, D. Angew. Chem., Int. Ed. 2011, 50, 12008
24. Belmar, J.; Funk, R. L. J. Am. Chem. Soc. 2012, 134, 16941
25. Artman, G. D., III; Weinreb, S. M. Org. Lett. 2003, 5, 1523
26. Fuchs, J. R.; Funk, R. L. J. Am. Chem. Soc. 2004, 126, 5068
27. Sabahi, A.; Novikov, A.; Rainier, J. D. Angew. Chem., Int. Ed. 2006, 45, 4317
28. Evans, M. A.; Sacher, J. R.; Weinreb, S. M. Tetrahedron 2009, 65, 6712
29. Wu, H.; Xue, F.; Xiao, X.; Qin, Y. J. Am. Chem. Soc. 2010, 132, 14052
30. Schammel, A. W.; Chiou, G.; Garg, N. K. Org. Lett. 2012, 14, 4556
31. Ishida, T.; Takemoto, Y. Tetrahedron 2013, 69, 4517
32. Ishida, T.; Ikota, H.; Kurahashi, K.; Tsukano, C.; Takemoto, Y. Angew. Chem., Int. Ed. 2013, 52, 10204
33. Zhang, H.; Hong, L.; Kang, H.; Wang, R. J. Am. Chem. Soc. 2013, 135, 14098
34. Krishnan, S.; Stoltz, B. M. Tetrahedron Lett. 2007, 48, 7571
35. Ma, S.; Han, X.; Krishnan, S.; Virgil, S. C.; Stoltz, B. M. Angew. Chem., Int. Ed. 2009, 48, 8037
36. Fuchs, J. R.; Funk, R. L. Org. Lett. 2005, 7, 677
37. Dou, X.; Yao, W.; Zhou, B.; Lu, Y. Chem. Commun. 2013, 49, 9224
38. Marfat, A.; Carta, M. P. Tetrahedron Lett. 1987, 28, 4027
39. Snider, B. B.; Busuyek, M. V. Tetrahedron 2001, 57, 3301
40. Gareau, Y.; Zamboni, R.; Wong, A. W. J. Org. Chem. 1993, 58, 1582
41. Voelker, T.; Ewell, T.; Joo, J.; Edstrom, E. D. Tetrahedron Lett. 1998, 39, 359
42. Fukuyama, T.; Liu, G. J. Am. Chem. Soc. 1996, 118, 7426
43. Trost, B. M.; Malhotra, S.; Chan, W. H. J. Am. Chem. Soc. 2011, 133, 7328
44. Li, P.; Buchwald, S. L. Angew. Chem., Int. Ed. 2011, 50, 6396
45. Wang, Y.; Kong, C.; Du, Y.; Song, H.; Zhang, D.; Qin, Y. Org. Biomol. Chem. 2012, 10, 2793
46. Yamada, Y.; Arima, S.; Okada, C.; Akiba, A.; Kai, T.; Harigaya, Y. Chem. Pharm. Bull. 2006, 54, 788